Nice post matey.

There are a load of positives to take from that experience.

Drinking is a vice of mine too. Its way too easy to get drunk when all your mates are around. If not from boredom or habit from your friends actively encouraging you.

As far as the hb8 maybe a more direct approach would have worked. You say you want to work your way in through the friend? I'm not sure that's such a great idea. Leaving aside that it will have been tried a million times, is your game good enough to move from the friend to the target? The friend will smell it coming a mile off and become a huge obstacle. No one likes to be used like that. My bet is you end getting off with the friend if anything.

In a club full of drunks, why not be the guy that strolls up and says 'Hi, I don't think we've met, I'm covert operation'? In a situation were she's the only hot girl in the club any approach is going to be a direct approach anyway.

If you don't have the balls for that yet(and neither do I) I'm fond of the old "Hay are you girls rich?" I'm looking for a rich girl to look after me. Buy me drinks, take me out......improv from there. If they really don't want to be approached it will die on its arse but its usually enough to get a convo going.